GB688087A - Improvements in or relating to the manufacture of organosilicon compounds - Google Patents
Improvements in or relating to the manufacture of organosilicon compoundsInfo
- Publication number
- GB688087A GB688087A GB174251A GB174251A GB688087A GB 688087 A GB688087 A GB 688087A GB 174251 A GB174251 A GB 174251A GB 174251 A GB174251 A GB 174251A GB 688087 A GB688087 A GB 688087A
- Authority
- GB
- United Kingdom
- Prior art keywords
- silicon
- ethyl
- reaction
- hydrocarbon
- dimethyldichlorosilane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003961 organosilicon compounds Chemical class 0.000 title 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 6
- 239000010703 silicon Substances 0.000 abstract 6
- 229910052710 silicon Inorganic materials 0.000 abstract 6
- 239000005046 Chlorosilane Substances 0.000 abstract 5
- -1 alkyl aryl chlorosilanes Chemical class 0.000 abstract 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 4
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 abstract 4
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 abstract 4
- 229930195733 hydrocarbon Natural products 0.000 abstract 4
- 150000002430 hydrocarbons Chemical class 0.000 abstract 4
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical group C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 abstract 4
- 239000000203 mixture Chemical group 0.000 abstract 4
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical group CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- FQEKAFQSVPLXON-UHFFFAOYSA-N butyl(trichloro)silane Chemical class CCCC[Si](Cl)(Cl)Cl FQEKAFQSVPLXON-UHFFFAOYSA-N 0.000 abstract 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 abstract 2
- 239000005055 methyl trichlorosilane Substances 0.000 abstract 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 abstract 2
- 239000005049 silicon tetrachloride Substances 0.000 abstract 2
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical group Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 abstract 2
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 abstract 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 229910000519 Ferrosilicon Inorganic materials 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910045601 alloy Inorganic materials 0.000 abstract 1
- 239000000956 alloy Substances 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- KWYZNESIGBQHJK-UHFFFAOYSA-N chloro-dimethyl-phenylsilane Chemical compound C[Si](C)(Cl)C1=CC=CC=C1 KWYZNESIGBQHJK-UHFFFAOYSA-N 0.000 abstract 1
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 abstract 1
- PNECSTWRDNQOLT-UHFFFAOYSA-N dichloro-ethyl-methylsilane Chemical compound CC[Si](C)(Cl)Cl PNECSTWRDNQOLT-UHFFFAOYSA-N 0.000 abstract 1
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000005048 methyldichlorosilane Substances 0.000 abstract 1
- 229940038384 octadecane Drugs 0.000 abstract 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- 239000005054 phenyltrichlorosilane Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 1
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000005051 trimethylchlorosilane Substances 0.000 abstract 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C07F7/16—Preparation thereof from silicon and halogenated hydrocarbons direct synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/122—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving the formation of Si-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
Alkyl- and/or alkyl aryl chlorosilanes are prepared by reacting an aliphatic hydrocarbon with silicon and a chlorosilane of the formula RnSiCl4-n, where n is 0 or 1 and R is an alkyl or phenyl radical, or a mixture of such chlorosilanes at a temperature of from 200 DEG to 600 DEG C. and at a pressure of at least 75 lbs./sq. inch. The preferred reaction temperature range is from 275 DEG to 500 DEG C. The hydrocarbon may be a saturated or unsaturated hydrocarbon, e.g. any hydrocarbon of the series methane to octadecane, ethylene, isobutylene, di-isobutylene, acetylene, butadiene or octadecene or mixtures of these hydrocarbons. The chlorosilane may be silicon tetrachloride and phenyl-, methyl-, ethyl- and octadecyl-trichlorosilane. The silicon may be used in the form of an alloy, e.g. ferrosilicon, or it may contain impurities such as carbon, iron, aluminium or calcium. Preferably the silicon has a particle size of less than 20 mesh per inch. Aluminium chloride, boron trifluoride or boron trichloride may be used to catalyse the reaction, e.g. in a proportion of from 0.1 mol. per cent to 15 mol. per cent based on the total mols. of hydrocarbon and chlorosilane. In the examples: (1) methyl- and ethyl-trichlorosilane and dimethyldichlorosilane are obtained from the reaction of silicon, methane and silicon tetrachloride; (2) ethyl-, propyl- and butyl-trichlorosilanes and dimethyldichlorosilane are obtained as in (1) from diisobutylene; (3), (4) using heptane instead of methane in (1) gives a mixture of methyl and ethyl trichlorosilanes, and a mixture of methyl-, ethyl-, propyl- and butyl-trichlorosilanes; (5) methyldichlorosilane, ethyl trichlorosilane, dimethyldichlorosilane, trimethylchlorosilane and ethylmethyldichlorosilane are obtained from the reaction of silicon, heptane and methyltrichlorosilane; (6), (7) using the procedure of (1) with aluminium chloride and boron chloride respectively as the catalysts, methyltrichlorosilane is formed; (8) phenylmethyldichlorosilane, phenyldimethylchlorosilane and dimethyldichlorosilane are obtained from the reaction of methane, silicon and phenyltrichlorosilane.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE508438D BE508438A (en) | 1951-01-23 | ||
| GB174251A GB688087A (en) | 1951-01-23 | 1951-01-23 | Improvements in or relating to the manufacture of organosilicon compounds |
| FR1046461D FR1046461A (en) | 1951-01-23 | 1951-12-15 | Manufacture of organosilicon compounds |
| DED11364A DE917248C (en) | 1951-01-23 | 1952-01-16 | Process for the preparation of alkyl and alkylarylchlorosilanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB174251A GB688087A (en) | 1951-01-23 | 1951-01-23 | Improvements in or relating to the manufacture of organosilicon compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB688087A true GB688087A (en) | 1953-02-25 |
Family
ID=9727205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB174251A Expired GB688087A (en) | 1951-01-23 | 1951-01-23 | Improvements in or relating to the manufacture of organosilicon compounds |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE508438A (en) |
| DE (1) | DE917248C (en) |
| FR (1) | FR1046461A (en) |
| GB (1) | GB688087A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008002164A1 (en) * | 2008-06-02 | 2009-12-03 | Wacker Chemie Ag | Process for the conversion of silicon tetrachloride or mixtures of silicon tetrachloride and dichlorosilane with methane |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2379821A (en) * | 1942-12-30 | 1945-07-03 | Du Pont | Compounds |
| US2405019A (en) * | 1943-10-05 | 1946-07-30 | Plax Corp | Process of making organo-silicon compounds containing a c-si bond |
-
0
- BE BE508438D patent/BE508438A/xx unknown
-
1951
- 1951-01-23 GB GB174251A patent/GB688087A/en not_active Expired
- 1951-12-15 FR FR1046461D patent/FR1046461A/en not_active Expired
-
1952
- 1952-01-16 DE DED11364A patent/DE917248C/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE917248C (en) | 1954-08-30 |
| FR1046461A (en) | 1953-12-07 |
| BE508438A (en) |
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